Fine Print
by ksfd89
Summary: A smutty oneshot set in Summer of AYITL because it's not right that Rory and Jess have never slept together. Possibly slightly OOC but fun to write! Hope you enjoy it!


**A smutty oneshot set in Summer of AYITL. Hope you enjoy!**

The Gazette is closed for the night, but Rory has stayed late. She's sorting through some articles for tomorrow - not that there's any rush - and having one last drink of whisky. A knock on the window makes her jump and she looks up to see Jess grinning at her.

"Jeez, you scared me," Rory complains as she opens the door to let him in. "What are you doing here?"

"Well hello to you too. I was walking past and saw you in the office. Isn't it late to be working?"

"Old habits die hard," Rory says, making Jess chuckle. "I just wanted to get a jump on things."

Jess nods, taking in the sight of the computer, and asks, "Any leads?"

"It's a hard choice between Taylor's pageant and the deal going on for snowcones," Rory says wryly. "But as long as I keep the poem on the front page the masses are happy."

"I remember when there was a run of snowcones," Jess says seriously. "Caused some real chaos."

"Not you for once, then?" Rory asks, smiling. Jess grins back, taking the chair opposite the desk.

"Even hoodlums have to take some time off."

"Is that right?"

Jess nods seriously and Rory gets out the spare glass, pouring Jess some whisky.

"Here. We should have a drink before you leave."

"Cheers," Jess says, lifting his glass to hers. "You know, I was going to ask you to dinner."

"You were?" Rory asks, caught off-guard and Jess nods, sounding shy as he says, "Yeah. But I thought maybe it would be awkward."

"It would've been fun," Rory says. "Where would we have gone?"

"Not sure," Jess admits. "Nowhere with _garden_ in the name at least."

"I remember your disdain for that," Rory grins. "You'd be safe here - you know Stars Hollow doesn't have the biggest range of restaurants."

"We could've explored out of town," Jess retorts. "Think a little wider, Gilmore. I wasn't going to take you to Luke's."

Rory giggles at that. "Hey, don't be too hard on the diner. Luke makes some mean pie."

"That he does," Jess admits and shrugs shyly as Rory asks, "So what would we have talked about?"

"Anything...the past four years? Five?"

"It doesn't feel that long since I saw you," Rory says and Jess nods.

"For me either."

"This whole year would require a bottle of wine," Rory says gloomily. Jess looks at her for a moment and then says, "Wait there."

"Where are you going?" Rory calls but Jess has already left the building and is hastening across the street. Rory sits, nonplussed, until the door opens and Jess comes back with a bag he is cradling carefully in his hands.

"Dinner is served," he announces. Placing the bag on the table, he takes out a pie and a large bottle of wine along with two forks. Rory laughs out loud.

"Where did this come from?"

"Luke's," Jess says, sitting back down. "Well, the wine's mine. I was going to take it to this work thing I have but screw it, I'll buy another bottle. The pie's cherry - hope that's good."

"Jess," Rory says as Jess starts cutting into it. "I can't believe you did this!"

"I know it's not a real dinner, but -"

"No, I love it," Rory says firmly. "This is so sweet Jess."

"I have my moments," Jess says. "Although apparently not a lot of sense. I forgot plates!"

"Here," Rory says, pulling out some papers from the shelf behind her. "Backcopies - no one will care if I throw them out."

"Then here's our meal." Jess cuts Rory a large slice of pie with a fork and, as he passes it over, Rory grins and takes a piece with her hand.

"Wow," she says happily. "That's still so good."

"I remember the forks and you use your fingers?" Jess scolds, passing Rory a napkin.

"Hey man, we're talking about pie!"

"Yes we are."

Jess grins at Rory, digging into his own slice. For a few moments both eat silently until Rory sits back and sighs.

"Hey, remember that night I helped you study and we had pie then too?"

"Remember, are you kidding? I think about that night all the time."

"Really?"

"Not constantly," Jess clarifies. "But I remember it pretty clearly for something that happened fourteen years ago. And how we went to get icecream."

"In _cones_," Rory teases, imitating Jess's voice, but then she groans. "Oh God - fourteen years ago!"

"Time does that annoying thing of passing."

"Fourteen years ago," Rory says miserably. "Man. Back then I thought my life was going somewhere too."

"Hey," Jess says gently, scooting his chair forward. "It still is."

Rory shrugs, her light mood gone. In response, Jess opens the bottle of wine, pouring each a generous portion in the glasses Rory hands him. She takes a large gulp as Jess asks, "You want to talk about it?"

"I told you before. I'm going nowhere."

"And I told you before," Jess says, "that it's a rut."

"It's okay to be in a rut when you're in your early twenties, not now!"

"Not true."

Rory stares at her hands before saying, "Back then I had a really clear plan. I knew where I was going and what I was doing and now -"

"Things change when you get older," Jess finishes for her. "It's not as simple. Remember what a punk I was back then? All I had figured out was that I wasn't going to waste my time in high school!"

"But look where you are now - somewhere great."

"And it took a lot of screwing up along the way," Jess says seriously. "Life has ups and downs, Rory. It's not a straight road."

Rory stares at him and Jess coughs. "Sorry - think I channelled Luke's self-help book there."

"What?" Rory asks, laughing and Jess groans and blushes.

"Man, it was million years ago now. Luke made me swear never to tell you guys - you and Lorelai."

"Tell us what?" Rory asks. "Come on Jess, it was years ago! Tell me!"

"Fine, you wore me down. When Luke started dating your mom he got this self-help book about relationships - I guess he was shy and wanted to communicate in something other than grunting, if you can imagine that. Anyway, when I came back to town for Liz's wedding he gave it to me."

"To _you?"_

"I don't know if you've noticed, but communication wasn't my strong point either."

Rory stares at Jess, memory clearing in her mind.

"Jess...that was when I was in Yale."

"When you were finishing your first year," Jess confirms and Rory gasps.

"When you asked me to go with you."

"I wasn't going to ask you that," Jess says, leaning forward. "Or I - I didn't know what I was going to say to you. I just wanted to tell you that I hadn't been fair to you; how I left without saying anything, how I told you I loved you and ran. I wanted to tell you that and see if we could try something. But when I saw Dean there I panicked, I guess. If I could do it over..."

"If _you_ could do it over." Rory shakes her head, letting out a dry laugh and Jess looks slightly hurt. "Jess, I'm not laughing at you, I'm laughing at me."

"Why?"

"You know how Dean was there? I was kind of getting into something with him. I'd had a really, really bad year, I was so lonely and everyone was making fun of me for not having a boyfriend for months. I was miserable. And then I started hanging out with Dean again and he was unhappy too - he'd got married and it wasn't working out."

"Shocker," Jess says drily but he lets Rory continue. She takes a deep breath and goes on, "When I was with him, it was like being young again. I mean, I was stupidly young then too, but it was like before I left home and when we were first dating. He made me feel safe. I felt comfortable with him. And you kind of freaked me out, when you asked me to go, and I think it pushed me to Dean more. Anyway, we were talking a lot, and then when Mom opened her inn I went home to get some CDs and Dean came over. And I slept with him."

Rory looks nervously at Jess who is looking at her with concern and asks, "Then what happened?"

"Then Mom came back and caught us - not right away but she knew when she saw us. It was awful, the whole thing. It was my first time. I was so happy and then she said all this stuff about how it wasn't okay and she was right, but I just didn't want to hear it. I went to Europe with Grandma for the summer, to get away from it all, and I wrote to tell Dean we couldn't be together and his wife found the letter. And he left her and we stayed together for a while but it wasn't good. I just wanted things to be how they were and it wound up with Dean dumping me at a party."

Rory lets out a bitter laugh and says, "I guess I didn't just start messing up, huh?" She takes a long drink of wine, embarrassed, and Jess puts his hand on her arm.

"Hey. You were so young."

"And stupid."

"You were young and stupid - welcome to the club. Everyone has stuff they wishes they could do over, and anyone who says they don't are either lying or are too scared to do anything."

"I knew it wasn't working with Dean, even back then. I just wanted it so much that I didn't brave moving forward. Dean told me it was over with Lindsey, his wife, that night, but I didn't push him on it. I just wanted it to be true so badly that I didn't think. Maybe I should have gone with you, who knows."

"No. We were so young - Rory, I still had to figure out my life. The place I was living in was a total sty."

"Maybe it would have been good for little while," Rory says, her voice a little wistful. "But you're right, I know. I thought I was an adult but I was still such a kid."

"We can't go back in time, Rory. To paraphrase Luke's book, we can only go forward."

"I'm not making great choices right now. And I keep wanting to move forward but it's like I'm stuck."

"What kind of choices?"

"I've been seeing Logan," Rory admits. "Remember him? When he's around I go to his place and sleep with him. He's engaged to this French heiress but he says he doesn't really love her, that it was arranged. I don't think it's just me he sleeps with besides her. God, when I say it out loud it sounds awful - because it is, I know. It's like I can't let go of him."

"Yes you can," Jess says seriously. "I know you can. You're going through some stuff right now and it's got you thinking that you can't break out of it. But you're stronger than that."

"You think so?"

"I know so."

"I'm not so great at ending things," Rory admits. "He's been in my life for so long."

"That jerk with the porsche?"

Rory nods, smiling slightly at the description. "That's the one. When I met him he turned my world upside down. Man, that sounds so cheesy, I know, but he did. It was like an adventure, being with him."

"More of an adventure than Dean, huh?" Jess asks wryly and Rory laughs.

"Just a little. And when I see him, even now, it still feels that way. But it's funny, you describing Logan like that - when I went out with that time, and him, I was starting to see more to him. He was losing his charm a little, I guess. And when you said all that stuff about Logan I wanted to defend him but I couldn't, because it was true. And I knew it."

_Just like with Mom and Dean_, Rory thinks, but she doesn't voice it. Instead she finishes her glass of wine and says, "Sometimes I think about doing that differently too - that I should have broken up with him then. And Jess, I've always meant to thank you, for that night."

"How come?"

"You got me to go back to Yale."

"You got yourself back to Yale," Jess corrects and Rory smiles.

"I don't know if I would have without what you said. I'm sorry we couldn't have dinner alone like we wanted, that night."

"Same. I think about how I wanted to call you again," Jess says, "Back at that time - I wanted to talk to you some more, only I thought you should have space. I wish I'd called. But I think more about how I messed up at your dorm, the night I ran into you and Dean. What I wanted to say instead."

"What would you have said if you could do it differently?"

"I'd say I was sorry," Jess says, letting out a deep breath. "I'd say...I'd say I still love you, but it was wrong to drop it on you like that. I got scared and bolted - kind of a pattern."

"For me too," Rory admits. "And I'd say...I'd say I forgive you."

"Really?"

"I forgave you years ago, Jess," Rory says softly. "Do you - have you forgiven me?"

"For what?"

"For kissing you at Truncheon," Rory says. She wants to duck her gaze but forces herself to keep looking into Jess's eyes. "For being such a jerk."

"I do. I have."

"I'm not trying to make an excuse, but I didn't go there planning to do it - only no, I kind of did," Rory says, shaking her head. "That's an excuse too. I wanted to see you, tell you how proud I was, and that's true, I swear. But was also mad at Logan for cheating on me, even though he said it wasn't cheating, and I wanted to hurt him back. And I felt there was something between us, and I thought maybe something could happen. And I'm so sorry."

"Something could've happened," Jess says. "Something could have always happened between us."

Rory's breath tightens. She stares into Jess's eyes but settles on simply saying, "I'm sorry. I shouldn't have done what I did. You were right when you said you didn't deserve it. I was terrible."

"I forgave you so many years ago, Rory," Jess says. "I was mad at you but I forgave you that same night."

"You did?"

"Maybe not that night, but pretty close," Jess admits and Rory laughs. Suddenly, Jess gets up and draws the blinds across the windows.

"What are you doing?" Rory asks in surprise and Jess says, "Hey, I might not have lived here for a long time but I remember the gossip mill. If people see us sitting in here we'll be the ones ending up front page news."

"Drinking, nonetheless," Rory laughs. "Better lock the door too. Speaking of drinking, do you want another glass?"

"Fill it up, Gilmore."

Rory obliges. They drink silently until Rory puts her glass down and says, "Thank you."

"For what?"

"Being here, listening to me ramble, giving such great advice."

"No one I'd rather listen to. And the advice I give I don't always follow."

"It's still good. And thank you."

"You're welcome," Jess says sincerely. "It's good seeing you, Rory."

"You know, even though it's been maybe four years since we last hung out, it doesn't feel like it. It never feels like a long time since I last saw you."

"For me either," Jess agrees. "With most people, it's usually an awkward smalltalk deal but with you..."

"We just pick up where we left off," Rory finishes for him. Jess grins at her and Rory doesn't know if it's his smile, the wine or just being with Jess that makes her say, "It's too bad we never slept together back then. I think it would have been hot."

"You think?"

"I know," Rory says, making Jess laugh. "Don't you?"

"I'm pretty sure," Jess answers. He's smiling at her, staring into her eyes and without thinking Rory leans across the desk and kisses him. She almost instantly breaks it, clapping a hand over her mouth, but then Jess is going around the desk and kissing her back, holding Rory tightly in his arms.

"Jess," Rory gasps. "Should we - are we -?"

"I want to," Jess says in a low voice and Rory nods, smiling.

"Let's pick up where we left off."

They kiss and kiss, unsurely and then passionately. Rory is clinging to Jess's neck, his strong arms tight around her back and she groans as he keeps one hand there and runs another slowly through her hair. If she was able to talk she'd tease him if that was the reason he closed the blinds, but Rory isn't feeling very capable of speech right now. All she can think about is kissing him. Jess breaks away, making her pant, and says, "Rory, are you sure about this?"

"More than sure."

"I don't want us to do something you'll regret."

"I am not going to regret this," Rory says firmly. "Are you?"

"No," Jess says, putting his hands around Rory's waist. "No way."

He kisses her again, hesitantly and then desperately. Rory moves her hands to Jess's hips, caressing them and daring to slip her hands under his shirt. Jess groans as Rory feels his taut skin and then is pulling his shirt off, before moving to Rory's. She helps him unclasp her bra and then gasps as Jess starts kissing her breasts, circling her nipples with his tongue.

"Oh, Jess!"

"Is that okay?" he asks gently and Rory pants, "Don't stop."

Jess doesn't. He kisses Rory all over, hard and throbbing between her legs, and Rory knows her underwear is soaked already. Impatiently she tugs at Jess's waistband and obligingly he pulls off his pants before moving to hers. Rory is so desperate for him to keep kissing that she practically falls off the desk as she wriggles her pants off, making both of them laugh, and again as the wine bottle topples.

"Moment killer?" Rory asks sheepishly and Jess shakes his head.

"No way."

They are both down to their underwear now and look shyly at each other.

"Should we slow it down?" Jess asks carefully and Rory rigorously shakes her head.

"Not unless you want to."

Jess answers her with a kiss. Rory wraps her legs around his, desperate for him to thrust into her, but instead Jess keeps kissing her chest, down to her legs and her underwear which he eases off before slipping his fingers there. Rory pants breathlessly as Jess drops to his knees, taking his hand away so he can kiss her there instead and she moans as he makes unbearably slow circles with his tongue.

"Jess, please!"

He keeps on steadily until Rory comes with a loud cry. Finally Jess straightens up, smiling, but before he can speak Rory is sitting up and grabbing him, running her hand up and down, guiding him inside her and making Jess gasp. He kisses her neck, his breath hot against Rory's flushed skin, before moving, slowly and building to a fast rhythm which makes Rory and the desk shake. They are both panting, staring into each other's eyes until finally Jess comes, shuddering onto her chest. Rory's legs are locked around his hips and she keeps them there until she feels herself come too, rushing around him. Slowly, Rory releases her legs and Jess smiles at her.

"Hi."

"Hi."

They kiss and Jess slowly slips out her before lying beside Rory on the desk.

"Wow."

"I'd say that was a fair assessment."

"Hot?" Jess teases and Rory grins.

"Hotter than I could ever have imagined, Mariano."

Jess reaches to run his hand through Rory's hair and she smiles, catching his hand in hers.

"It was amazing."

"No argument."

Rory looks around at the mess they've made and giggles.

"Guess we should clean up. I don't know how I'm going to explain this in the morning."

"We can leave it a little longer," Jess says, kissing her shoulder and Rory smirks.

"Oh yeah?"

"Yeah. Time to talk...and other stuff too."

"Other stuff, huh?"

"I think you'll like it."

"I'm sure," Rory laughs. "You know, one thing definitely hasn't changed."

"And what's that?"

"We do a great job of breaking the rules."

"That we most certainly do."

"What time are you leaving?"

"Not until afternoon."

"Well, that gives ample time for icecream," Rory says seriously and Jess nods, breaking into a smile.

"In cones!"


End file.
